CN1323775A - 制备d,l－薄荷醇的方法 - Google Patents

制备d,l－薄荷醇的方法 Download PDF

Info

Publication number: CN1323775A
Authority: CN; China
Prior art keywords: menthol; hydrogen; isomenthol; catalyzer; reactor
Prior art date: 2000-05-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

CN01116906A

Other languages

English (en)

Chinese (zh)

Inventor

A·施莱梅纳特

R·兰格

C·德雷斯巴赫

H·-J·格罗斯

T·普林茨

A·舒尔策－蒂林

M·弗里德里希

J·D·詹特施

G·约翰

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-05-12

Filing date

2001-05-11

Publication date

2001-11-28

2001-05-11 Application filed by Bayer AG filed Critical Bayer AG

2001-11-28 Publication of CN1323775A publication Critical patent/CN1323775A/zh

Status Pending legal-status Critical Current

Links

NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 title claims abstract description 118
238000000034 method Methods 0.000 title claims abstract description 51
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims abstract description 156
229940041616 menthol Drugs 0.000 claims abstract description 58
239000000203 mixture Substances 0.000 claims abstract description 57
239000003054 catalyst Substances 0.000 claims abstract description 28
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 22
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 22
238000006317 isomerization reaction Methods 0.000 claims abstract description 15
239000000463 material Substances 0.000 claims abstract description 13
230000008569 process Effects 0.000 claims abstract description 13
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract 4
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 44
NOOLISFMXDJSKH-LPEHRKFASA-N Isomenthol Natural products CC(C)[C@@H]1CC[C@H](C)C[C@H]1O NOOLISFMXDJSKH-LPEHRKFASA-N 0.000 claims description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
239000007787 solid Substances 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
239000003513 alkali Substances 0.000 claims description 7
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
239000011135 tin Substances 0.000 claims description 5
239000011701 zinc Substances 0.000 claims description 5
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
230000007704 transition Effects 0.000 claims description 4
229910052718 tin Inorganic materials 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
239000011148 porous material Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 21
230000003197 catalytic effect Effects 0.000 abstract 1
229910052593 corundum Inorganic materials 0.000 abstract 1
229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
239000002994 raw material Substances 0.000 description 36
239000000047 product Substances 0.000 description 26
238000005984 hydrogenation reaction Methods 0.000 description 15
239000007791 liquid phase Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
150000002431 hydrogen Chemical class 0.000 description 12
239000000243 solution Substances 0.000 description 12
238000004821 distillation Methods 0.000 description 9
-1 l-menthol compound Chemical class 0.000 description 9
230000009467 reduction Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000004215 Carbon black (E152) Substances 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 8
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 7
NOOLISFMXDJSKH-OPRDCNLKSA-N Isomenthol Chemical compound CC(C)[C@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-OPRDCNLKSA-N 0.000 description 7
235000016257 Mentha pulegium Nutrition 0.000 description 7
235000004357 Mentha x piperita Nutrition 0.000 description 7
238000001035 drying Methods 0.000 description 7
235000001050 hortel pimenta Nutrition 0.000 description 7
229930007461 neoisomenthol Natural products 0.000 description 7
239000012071 phase Substances 0.000 description 7
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 7
241001479543 Mentha x piperita Species 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
238000005194 fractionation Methods 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000002245 particle Substances 0.000 description 6
230000003245 working effect Effects 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000001764 infiltration Methods 0.000 description 5
230000008595 infiltration Effects 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
239000005844 Thymol Substances 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
238000009434 installation Methods 0.000 description 4
238000011068 loading method Methods 0.000 description 4
239000011572 manganese Substances 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
230000006340 racemization Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229960000790 thymol Drugs 0.000 description 4
238000005406 washing Methods 0.000 description 4
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910002651 NO3 Inorganic materials 0.000 description 3
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
150000003818 basic metals Chemical class 0.000 description 2
239000011324 bead Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
230000002779 inactivation Effects 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910052761 rare earth metal Inorganic materials 0.000 description 2
150000002910 rare earth metals Chemical class 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
230000001835 salubrious effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
NFLGAXVYCFJBMK-IUCAKERBSA-N (-)-isomenthone Chemical compound CC(C)[C@@H]1CC[C@H](C)CC1=O NFLGAXVYCFJBMK-IUCAKERBSA-N 0.000 description 1
WUOACPNHFRMFPN-VIFPVBQESA-N (R)-(+)-alpha-terpineol Chemical compound CC1=CC[C@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-VIFPVBQESA-N 0.000 description 1
YSTPAHQEHQSRJD-UHFFFAOYSA-N 3-Carvomenthenone Chemical compound CC(C)C1CCC(C)=CC1=O YSTPAHQEHQSRJD-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000004278 EU approved seasoning Substances 0.000 description 1
235000006679 Mentha X verticillata Nutrition 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000002899 Mentha suaveolens Nutrition 0.000 description 1
235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
KRSZDIGCQWBYNU-UHFFFAOYSA-N [Mn].[Ru] Chemical compound [Mn].[Ru] KRSZDIGCQWBYNU-UHFFFAOYSA-N 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052728 basic metal Inorganic materials 0.000 description 1
229910001038 basic metal oxide Inorganic materials 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical group [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000007599 discharging Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
NFLGAXVYCFJBMK-UHFFFAOYSA-N isomenthone Natural products CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
229930006968 piperitone Natural products 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000002912 waste gas Substances 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/12—Menthol
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/96—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the noble metals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CN01116906A 2000-05-12 2001-05-11 制备d,l－薄荷醇的方法 Pending CN1323775A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10023283.3		2000-05-12
DE10023283A DE10023283A1 (de)	2000-05-12	2000-05-12	Verfahren zur Herstellung von d,l-Menthol

Publications (1)

Publication Number	Publication Date
CN1323775A true CN1323775A (zh)	2001-11-28

Family

ID=7641784

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN01116906A Pending CN1323775A (zh)	2000-05-12	2001-05-11	制备d,l－薄荷醇的方法

Country Status (6)

Country	Link
US (1)	US20020019573A1 (ja)
EP (1)	EP1162186A3 (ja)
JP (1)	JP2001322960A (ja)
CN (1)	CN1323775A (ja)
DE (1)	DE10023283A1 (ja)
HK (1)	HK1040984A1 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103097019A (zh) *	2010-07-23	2013-05-08	朗盛德国有限责任公司	异构化催化剂
CN104307464A (zh) *	2014-10-24	2015-01-28	上海迅凯新材料科技有限公司	苯深度脱噻吩的钌基吸附剂及其制备方法和应用
CN111871428A (zh) *	2020-07-22	2020-11-03	上海应用技术大学	一种用于制备d,l-薄荷醇的铑催化剂及d,l-薄荷醇的制备方法
CN112844389A (zh) *	2021-02-03	2021-05-28	合肥工业大学	用于合成d,l-薄荷醇的钴镍合金催化剂的制备方法、制得催化剂及其应用

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102356055B (zh)	2009-02-17	2015-04-08	长冈实业株式会社	用于生产天然l-薄荷醇的方法和装置
EP2457554A1 (de) *	2010-11-24	2012-05-30	Symrise AG	Menthol enthaltende Mischung
EP2703376A1 (de)	2012-08-31	2014-03-05	LANXESS Deutschland GmbH	Verfahren zur Herstellung von Menthol
EP2703374A1 (de)	2012-08-31	2014-03-05	LANXESS Deutschland GmbH	Verfahren zur Herstellung von Menthol
DE102013203420A1 (de) *	2013-02-28	2014-08-28	Evonik Industries Ag	Hydrogenolyse von Furfurylalkohol zu 1,2-Pentandiol
RU2758864C1 (ru) *	2020-05-26	2021-11-02	Общество С Ограниченной Ответственностью "Научно - Исследовательский Институт Технологий Органической, Неорганической Химии И Биотехнологий"	СПОСОБ ПОЛУЧЕНИЯ d,l-МЕНТОЛА

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19853562B4 (de) *	1998-11-20	2006-06-08	Lanxess Deutschland Gmbh	Verfahren zur Herstellung von d,l-Menthol

2000
- 2000-05-12 DE DE10023283A patent/DE10023283A1/de active Pending
2001
- 2001-04-30 EP EP01110082A patent/EP1162186A3/de not_active Withdrawn
- 2001-05-08 US US09/850,971 patent/US20020019573A1/en not_active Abandoned
- 2001-05-09 JP JP2001139096A patent/JP2001322960A/ja active Pending
- 2001-05-11 CN CN01116906A patent/CN1323775A/zh active Pending
2002
- 2002-04-08 HK HK02102608.8A patent/HK1040984A1/zh unknown

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103097019A (zh) *	2010-07-23	2013-05-08	朗盛德国有限责任公司	异构化催化剂
CN104307464A (zh) *	2014-10-24	2015-01-28	上海迅凯新材料科技有限公司	苯深度脱噻吩的钌基吸附剂及其制备方法和应用
CN104307464B (zh) *	2014-10-24	2017-02-22	上海迅凯新材料科技有限公司	苯深度脱噻吩的钌基吸附剂及其制备方法和应用
CN111871428A (zh) *	2020-07-22	2020-11-03	上海应用技术大学	一种用于制备d,l-薄荷醇的铑催化剂及d,l-薄荷醇的制备方法
CN111871428B (zh) *	2020-07-22	2023-04-28	上海应用技术大学	一种用于制备d,l-薄荷醇的铑催化剂及d,l-薄荷醇的制备方法
CN112844389A (zh) *	2021-02-03	2021-05-28	合肥工业大学	用于合成d,l-薄荷醇的钴镍合金催化剂的制备方法、制得催化剂及其应用
CN112844389B (zh) *	2021-02-03	2022-06-07	合肥工业大学	用于合成d,l-薄荷醇的钴镍合金催化剂的制备方法、制得催化剂及其应用

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